[ CAS No. 55332-38-2 ] {[proInfo.proName]}

Name: 55332-38-2|(S)-2-(4-Chlorophenyl)-3-methylbutanoic acid|98%
Brand: Ambeed
SKU: A164384
Rating: 98 (26 reviews)

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2D 3D

Structure of 55332-38-2 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 55332-38-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 55332-38-2 ]

SDS Specification

Alternatived Products of [ 55332-38-2 ]

Product Details of [ 55332-38-2 ]

CAS No. :	55332-38-2	MDL No. :	MFCD04112625
Formula :	C₁₁H₁₃ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VTJMSIIXXKNIDJ-JTQLQIEISA-N
M.W :	212.67	Pubchem ID :	854132
Synonyms :

Safety of [ 55332-38-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 55332-38-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 55332-38-2 ]

[ 55332-38-2 ] Synthesis Path-Downstream 1~19

1
[ 86618-06-6 ]
[ 55332-38-2 ]
[ 63640-09-5 ]
[ 127641-48-9 ]
[ 197018-23-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In water for 22h; Ambient temperature; horse liver esterase, pH 7.2; Yield given. Yields of byproduct given;
	Yield given. Yields of byproduct given;

Reference： [1]Ahmar, M.; Girard, C.; Bloch, R. [Tetrahedron Letters, 1989, vol. 30, # 50, p. 7053 - 7056]
[2]Ahmar, M.; Girard, C.; Bloch, R. [Tetrahedron Letters, 1989, vol. 30, # 50, p. 7053 - 7056]

2
(2S,3R)-2-[2-(4-Chloro-phenyl)-3-methyl-butyryloxy]-3-hydroxy-succinic acid dimethyl ester [ No CAS ]
[ 55332-38-2 ]
[ 63640-09-5 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; acetic acid at 85℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Castaldi, Graziano; Cavicchioli, Silvia; Giordano, Claudio; Uggeri, Fulvio [Journal of Organic Chemistry, 1987, vol. 52, # 14, p. 3018 - 3027]

3
[ 33131-40-7 ]
[ 55332-38-2 ]
[ 63640-09-5 ]

Yield	Reaction Conditions	Operation in experiment
	With silver tetrafluoroborate; (S)-cyclohexyl-BINAP; hydrogen; triethylamine; rhodium(I) chloride In methanol at 25℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
	With silver tetrafluoroborate; hydrogen; triethylamine; (R)-2,2′-bis(dicyclohexylphosphino)-1,1′-binaphthyl; rhodium(I) chloride In methanol at 25℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
88% ee	With (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; hydrogen; cobalt(II) stearate In tetrahydrofuran; <i>tert</i>-butyl alcohol at 40℃; for 72h; Glovebox; Overall yield = 91 percent; enantioselective reaction;

Reference： [1]Takemoto, Ichiki; Kawamura, Norio; Kaminaka, Hiroshi [Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 11, p. 2071 - 2072]
[2]Takemoto, Ichiki; Kawamura, Norio; Kaminaka, Hiroshi [Bioscience, Biotechnology and Biochemistry, 1994, vol. 58, # 11, p. 2071 - 2072]
[3]Du, Xiaoyong; Xiao, Ye; Yang, Yuhong; Duan, Ya-Nan; Li, Fangfang; Hu, Qi; Chung, Lung Wa; Chen, Gen-Qiang; Zhang, Xumu [Angewandte Chemie - International Edition, 2021, vol. 60, # 20, p. 11384 - 11390][Angew. Chem., 2021, vol. 133, # 20, p. 11485 - 11491,7]

4
[ 2012-74-0 ]
[ 55332-38-2 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 2654 - 2658
[2]Journal of Agricultural and Food Chemistry,1999,vol. 47,p. 2145 - 2155

5
[ 18713-58-1 ]
[ 55332-38-2 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 1868 - 1869

6
[ 2012-74-0 ]
[ 2627-86-3 ]
[ 55332-38-2 ]

Reference： [1]Patent: WO2004/60850,2004,A1 .Location in patent: Page 15
[2]Patent: WO2004/60850,2004,A1 .Location in patent: Page 17
[3]Patent: WO2004/60850,2004,A1 .Location in patent: Page 17
[4]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16-20
[5]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16
[6]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16
[7]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16
[8]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16
[9]Patent: WO2004/60850,2004,A1 .Location in patent: Page 18
[10]Patent: WO2004/60850,2004,A1 .Location in patent: Page 17
[11]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16
[12]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16
[13]Patent: WO2004/60850,2004,A1 .Location in patent: Page 17
[14]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16-17
[15]Patent: WO2004/60850,2004,A1 .Location in patent: Page 17
[16]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16
[17]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16
[18]Patent: WO2004/60850,2004,A1 .Location in patent: Page 16
[19]Patent: WO2004/60850,2004,A1 .Location in patent: Page 17

7
[ 73591-05-6 ]
[ 71656-96-7 ]
[ 55332-38-2 ]
[ 63640-09-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In water; toluene at 60 - 78℃; for 0.5 - 0.666667h;	11A; 11B EXAMPLE-11 A The filtrate (2507g) and washings of wet cake (850g) obtained from above example of resolution of () CPA was concentrated under reduced pressure to remove solvent (butanol) at a temperature ranging from 60-78°C after which 200g of 40% Sulphuric acid was added to the residue and mixed thoroughly for 30-40 minutes at that stage, toluene (500g) was added and stirred further to extract the liberated (-) CPA acid into the toluene layer. The contents were transferred into a separator and the lower acidified aq. layer containing PEA-HS04 (RA-1; 407g) was separated and mixed with acidified aqueous layer obtained from (+) CPA recovery for liberating the resolving amine, as described in example (11 B). The toluene layer (733 g) was made free of traces of acid by washing with distilled water and concentrated under reduced pressure to obtain (-) CPA (320g) which was subsequently racemised. EXAMPLE-11 B The acidified aqueous layers (SA-1, 641G ; RA-1,407g) obtained after recovery of (+) CPA and (-) CPA respectively are mixed in a suitable reactor and cooled to 0°-5°C under constant stirring, 200g of 50% caustic lie was added over a period of 10-15 minutes and the layers were allowed to separate. The upper layer containing (204g) of crude PEA was separated and aqueous layer was extracted with toluene twice (2 x 100G) and the toluene layers were analysed for PEA content to be used for further batches of resolution of () CPA.
	With sulfuric acid In water; butan-1-ol at 60 - 70℃;	12 The mother liquor (ML-1,28. 319kg) and washing (WS-1 ; 10.02) obtained from above described resolution process of () CPA containing R enriched (-) CPA is fed into a Rotary evaporator equipped with vacuum system, and made free of butanol and water at a temperature of 60°-70°C under vacuum (21-6 mm) by addition of 5. 1kg of fresh distilled water during distillation. After ensuring the complete removal of solvent, 1.97 kg of 40% aqueous Sulphuric acid is fed into the reactor and mixed for 20-40 minutes, followed by addition of 5.08kg of toluene. The liberated (-) CPA-PEA sulfate solution is transferred into a 20.0 lit. glass stirred reactor and stirred for 20-30 minutes after which the layers were allowed to separate. The acidic aqueous layer containing (-) PEA-HS04 (RA-1; 4.2kg) is stored to be mixed with corresponding acidic aq. layer obtained from (+) CPA acid recovery to liberate (-) PEA. Toluene layer is washed with distilled water (3 x 3. 0KG) till pH of aqueous layer is neutral. These washings are stored for reuse in subsequent batches. Toluene layer (8.39kg) is concentrated in Rota evaporator, under vacuum (40-6mm) at temperature of 40-50°C to obtain 3.67kg (-) CPA which is dried in vacuum tray drier at 40-45°C to yield 3.3kg of (-) CPA which is subsequently racemised to () CPA. The acidified aqueous layers (SA-1,6. 4kg ; RA-1, 4.2kg) obtained from recovery of corresponding (+) CPA and (-) CPA are mixed and charged into 20.0 lit. glass stirred reactor and cooled to 10-5°C. 2.04kg of 50% caustic lye solution is added while stirring the contents in 60-75 minutes and the layers are allowed to separate out. Upper layer containing (-) PEA is separated out (2.14kg) and stored to be used for further batches of racemiation of (+) CPA. Aqueous layer is washed twice (2 x 2. 0KG) with toluene. Toluene layer was estimated for PEA content and recycled for further batches.

Reference： [1]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2004/60850, 2004, A1 Location in patent: Page 12-13
[2]Current Patent Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH (IN) - WO2004/60850, 2004, A1 Location in patent: Page 14

8
[ 4570-45-0 ]
[ 55332-38-2 ]
[ 1208552-68-4 ]